How to Peg Your Man for the First Time

There’s so much swag and accessories that goes along with pegging, it’s easy to skip past all the stuff you need to know in order to deal with how to try pegging and go straight for the shopping trips to get ready to peg your man for the first time. While the shopping is all well and good, there are 5 things you should know about your adventure into the wonderful world of pegging. We’re hoping to make your journey enjoyable for all parties involved.

Create a plan of action to peg your man.

So, your boyfriend casually mentions that he wants to try pegging. Here’s what NOT to do. Do not go out, buy the biggest strap-ondildo you can find and then stick it right up his bottom. Casually mentioning a desire to explore – and actually following through with it – are very, very different things. Before the two of you start pegging, you need to talk.

Find out how much knowledge and experience he has, if any at all. Talk about any concerns or insecurities that might accompany his desire to be pegged. You might feel insecure when asked to peg your man, believing that they aren’t satisfying their partner. But the pleasure men experience from prostate stimulation is simply different than what they enjoy from standard intercourse. Getting these conversations out of the way before you get started will make you both more comfortable and happy going in. Set up a plan of action going forward – schedule a trip to shop together, and to set up different sessions to explore pegging.

Start small.

Unless your man has a lot of experience with pegging, you will want to start off with a butt plug, toy or finger that is on the smaller size. Also remember it must have a flared base, where it’s wider at the top than where it goes in or it will easily just be swallowed alive. If this is the first time your partner has ever had anything put inside his butt, it’s a dangerous idea to leap straight to a full pegging. It’s dangerous for him because it can be painful, and it’s dangerous for you because you don’t know how much speed and force to use without causing your partner pain or tearing.

Before you step into your newly acquired strap-on dildo, work your way up, starting with some humble play to help prepare him for what’s to come. It will also give YOU a great anatomy lesson. Using your fingers to explore inside him until you find the prostate and learning to stimulate it will be great knowledge to have when you actually peg your man.

Lube it up – always – before you peg your man.

When you are in the heat of the moment, it is easy to forget lube; plus, if your partner seems open, you might think he doesn’t need lube at all. When it comes to pegging – or any kind of anal sex – the more lube, the better. The human anus has not one, but TWO sets of sphincters. There are the sphincters we can see externally, and then a second set deeper inside the anus.

Using lube makes your initial penetration through both sets of sphincters that much easier while creating a hot sense of friction. Just make sure the kind of lube you have purchased is compatible with your toys. The silicone based lube you have for your own playtime won’t work with your all of your toys – we suggest buying specialty water-based lube to use with toys only. That prevents the toy’s material from breaking down and potentially leaking chemicals into his body or yours.

Talk dirty.

Pegging isn’t just the act of penetrating a man with a with a strap-on dildo – it’s an entire sexual experience. Men love pegging because of the stimulation it gives to their prostate, but some men also love the role reversal that takes place when it’s a woman doing the work. It goes to follow then, that you should make the most of that role reversal. You’re dominating him when you’re pegging him, so dominate him with your dirty talk too! Test the waters by asking him if he likes the way something feels – you won’t know until you try. But don’t force it – if dirty talk while you peg isn’t for you, don’t pretend that it is.

Keep it clean when you peg your man.

You can be very dirty together and still remain hygienic. No toys that have been in his butt should ever go in your vagina unless they have been properly cleaned. Any bacteria that is picked up from the anus could be harmful to the vagina.

It’s also a good idea for him to anally douche with water before you begin to peg your man so that you have a fresh butthole to enjoy. Also, please remember to clean your sex toys before using them the first time, too! Fresh out of the package doesn’t always mean the thing is actually fresh. Safe is so much better than sorry, and if you do it right, you can turn your pre-washing of sex toys into a hot little foreplay game.

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